


Ruined Engagements

by SophiaTomlinson



Series: Supergirl Imagines [1]
Category: Supergirl (TV 2015)
Genre: F/M
Language: English
Status: Completed
Published: 2017-03-26
Updated: 2017-03-26
Packaged: 2018-10-10 21:09:36
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,661
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10447563
Author URL: https://archiveofourown.org/users/SophiaTomlinson/pseuds/SophiaTomlinson
Summary: You think that Winn is cheating on you with Kara, but in all reality shes helping him plan for what may be the most memorable night of his life.





	

From the moment that you met Winn Schott, you were instantly captured by him. You met him in your sophomore year of college. You were rushing to campus after sleeping over at a friend’s house, when you ran straight into him. Winn was fine, however you ended up getting a concussion with how hard you fell back and hit the concrete. He obviously took you to the hospital, no matter how many times you tried to tell him you were okay.

It was his day off of work so he stayed with you the whole time that you were in the hospital. The two of you had just clicked. You had talked about anything and everything, you had told him about your awkward middle school days, college life for you. He had told you all about his fabulous life as a foster care child. After that long day in the hospital, the two of you became basically attached at the hip; you even had a crush on him. Then, he started working at CatCo.

You were so proud of him for landing a job at CatCo, until Kara showed up. You couldn’t remember a time where you weren’t a little jealous of Kara Danvers. You were jealous of her before you even met her. You called yourself pathetic at first. Winn was allowed to have other friends besides you, you knew that. It was something about the way that he talked about her that nerved you.

The jealously got worse when you finally met Kara. Before you met her, your mind has conjured her up as this mean person, someone that it would be logical for you to not exactly like. However, when you actually met her, you couldn’t have been more off. Kara Danvers was one of the sweetest people you had ever met, plus you had to watch Winn make googly eyes at her the whole night.

You were with Winn through the whole Kara crush situation. You listened to him babble on and on about her all the time, and while it annoyed you to no end, you didn’t have the heart to stop him, no matter how much it hurt to listen to him talk about some other girl. Kara made him happy and you had to respect that. At least, that’s what you kept trying to convince yourself to think.

Then, one day, you decided to just admit your feelings. You were done listening to him talk about a girl who had absolutely no romantic interest in him. Let’s just say that it didn’t really go over all that well. After sitting in silence for what seemed like hours, he finally just asked you to leave. Apparently you admitting your feelings for him had inspired him to admit his feelings to Kara. It didn’t go well. When he was finally back from being kidnapped, you stood by him.

So, when Winn asked you out a few weeks later, you were shocked. After thinking for a moment, you denied him. You knew deep down that Winn still wasn’t completely over Kara. You told him that you would help him get over her, and that if by then, by the time he didn’t constantly think of the Kryptonian, he still felt the same, that you would be there; waiting.

It took Winn months to finally get over her, and you kept your promise. You helped him through the long months of getting over her. It hurt you to no end, watching him try and act like nothing had happened. It especially hurt when you found him hooking up with Siobhan in the closet at CatCo.

It all wasn’t for nothing though, the two of you ended up together in the end. After all of it, Kara had finally shown Winn that through everything, you were there. No matter what he had been going through, from his father to getting over what he thought could’ve been the love of his life, you were always there. Standing beside him and helping him through it. That’s when he decided that it was you he loved.

No matter how many times Winn had told you that he loved you, there was a small piece of you that still had this bad feeling when he was around her. You hated it, that you couldn’t bring yourself to truly trust the two of them alone together, but you pushed through it and just prayed that it would get better. That you’d eventually get over it.

After two years of being with him, you were sure that you had, and then the two of them started hanging out constantly. Now that Winn worked at the DEO, which already made him farther from you and closer to her, they then started to hang out outside of work more often than normal. At first it was just a drink here or there, but eventually it ended up spiraling into him spending hours with her, always making a big deal about how you couldn’t come.

Could you really blame yourself for getting suspicious? Your boyfriend and the girl that he used to be into were constantly hanging out, never letting you join. Obviously your mind had jumped to the worst conclusions. At first you let yourself just wallow in your own self doubt, until one day you finally let your true feelings come out. You probably shouldn’t have; it just led to an argument.

“Winn, can you really blame me for thinking that?! It’s been _weeks_ since you came straight home from work to spend time with me. I’m sorry that I’m a little upset.” You explain, trying to keep the tears from spilling out of your eyes and your voice from cracking. You watched as Winn opened his mouth to reply, but once his eyes finally landed on your figure, he rushed across the room to meet you.

“Hey, calm down, okay? I swear nothing is happening between Kara and I. I would never do that to you.” His voice is quiet yet strong, his hands cupping your face and his eyes staring straight into yours.

“Then what are you doing that you can’t tell me. It can’t be that important, please just tell me.” Your voice comes out, barely above a whimper as the tears threaten to spill over, eventually a few actually do. You watch as his eyes flicker over his face before he lets out a small sigh, his thumbs running over your cheeks, catching your tears.

“Give me a minute; I’ll be right back, okay?” He whispers to you, watching as your head slightly nods. Winn takes a step back before turning on his heels, heading down the hallway. You sniffle, your hands reaching up to run through your hair, pushing it back, away from your face as you wait for him to come back. Your eyes dart to him as he appears back in the living room, one of his hands behind his back.

“I can’t believe I’m doing this now after all the planning I did.” Winn mumbles incoherently, before stopping in front of you. You watch as his hand moves to come in between you. As your eyes land on the small box in his hand, you let out a small gasp, your eyes moving to look into his. You watch as Winn lets out a nervous laugh, before looking up to meet your eyes.

“This is what Kara and I have been up to. I’ve been trying to plan how I was going to propose to you. I wanted it to be perfect, so I rented out your favorite restaurant and I made a montage of all the moments we had together.” He mumbles, staring at you as your face falls, the feeling of regret washing over you. You ruined it, the proposal that he had been planning for months now, you ruined the surprise.

“I’m sorry Winn. I ruined everything. You had this whole event planned and now everything’s ruined.” You exhale.

“You didn’t ruin anything, alright? This is just happening a little sooner than I expected.” Winn explains, his empty hand reaching up to cup your face. As you open your mouth to speak, Winn cuts you off.

“I’m the one that should feel bad. You’re standing here on the verge of tears because I haven’t been paying attention to you like I should be. I shouldn’t have pushed you to the side. A perfect proposal isn’t worth losing you.” It’s your turn to cut him off.

“It’s still perfect Winn, because you’re the one proposing. It doesn’t matter where we are or what we’re doing. As long as you, the man I love, is the one asking, it doesn’t matter. We’ll just have an engagement party instead of a proposal.” You explain, a smile appearing on your face as you stare at him. You watch as Winn reciprocates your smile, before getting down on one knee.

“I’ll leave the speech for later then and get straight to it. Y/n, will you marry me?” His eyes twinkle as he says the words.

“Yes.” You reply, watching as he stands up before taking the ring out of the box, sliding it onto your finger. You pull his face towards yours, capturing his lips in a kiss. You begin to giggle happily as you pull away, finally getting a good look at the ring.

“Sorry it’s not bigger, it-” You smile, cutting him off with a peck.

“It’s perfect.” Winn smiles at you before pulling you into a passionate kiss, laughs coming from both of you as he picks you up and spins you in a circle. When he puts you down, you watch as he reaches over to pick up his phone.

“I guess I should tell Kara to let everyone know that the plans have changed.” He mumbles, and for the first time since you had found out about Kara, you didn’t have that bad feeling.


End file.
